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Alkynyl-containing ruthenium complex as well as synthesis method and application thereof

A technology of ruthenium complexes and synthesis methods, applied in the directions of ruthenium organic compounds, compounds containing elements of Group 8/9/10/18 of the periodic table, organic compounds/hydrides/coordination complex catalysts, etc. Cells do not have obvious cytotoxicity and other problems, and achieve significant anti-tumor activity, promote transmembrane absorption, and increase drug efficacy.

Inactive Publication Date: 2018-09-25
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such as [Ru(bpy) 2 (dppz)] 2+ Shows insignificant cytotoxicity to cancer cells despite strong binding ability to DNA

Method used

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  • Alkynyl-containing ruthenium complex as well as synthesis method and application thereof
  • Alkynyl-containing ruthenium complex as well as synthesis method and application thereof
  • Alkynyl-containing ruthenium complex as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] The synthesis of embodiment 1 ligand Br-DPPZ

[0075]

[0076] Weigh 315.16mg (1.5mmol) of o-phenanthroline 5,6-dione, 232.48mg (1.25mmol) of 4-bromo-o-phenylenediamine, add 20ml of absolute ethanol to a 30ml quartz tube, stir for 5 minutes, microwave React at 95°C for 3 minutes. After the reaction, cool to room temperature, add 30ml of water, a yellow-white solid precipitates, filter with suction, wash with water to obtain a filter cake, and dry in a vacuum oven at 50°C. Pure chloroform was dissolved, and pure chloroform was packed into a column, and the eluent was eluted with pure chloroform:dehydrated ethanol=100:1, and the main yellow band was collected, and the yellow solid was spin-dried under reduced pressure, and dehydrated alcohol:chloroform= 3:2 solvent for recrystallization. Yield: 80%.

Embodiment 2

[0077] Embodiment 2 [Ru(bpy) 2 (Br-DPPZ)] 2+ Synthesis

[0078]

[0079] In the 50ml three-neck bottle, put into appropriate ratio (1.5:1) of Br-DPPZ, [Ru(bpy) 2 Cl 2 ]·2H 2 O and ethylene glycol and water mixed solvent (V 乙二醇 :V 水 =9:1) 30ml, heat to reflux for 6 hours (T=120°C), stop the reaction, cool to room temperature, add 80ml of water to dilute, filter to obtain an orange-red clear filtrate, add excess NaClO to the filtrate 4 , producing a large amount of orange-red precipitate, which was filtered by suction and dried in a vacuum desiccator to obtain an orange-yellow crude product. The crude product was dissolved with a small amount of acetonitrile, purified and separated by a neutral alumina column, loaded with acetonitrile, and the main red component was washed with acetonitrile in an appropriate proportion, spin-dried under reduced pressure and then dried in a vacuum desiccator to obtain red crystals with a yield of 80% %.

Embodiment 3

[0080] Synthesis of Example 3 RM1601

[0081]

[0082] Weigh [Ru(bpy) 2 (BrDPPZ)] 2+ (125mg, 0.125mmol) in a 10ml microwave reaction tube (stirring bar was added to the tube), add 5ml of anhydrous acetonitrile supernatant to dissolve completely, under the protection of nitrogen, add appropriate amount of triethylamine (70μL, 0.501μmol) and phenylacetylene (70μL, 0.637 μmol), and then quickly add the catalyst Pd (PPh 3 ) 2 Cl 2 (17.6mg), CuI (20mg); after airtight, put into a microwave reactor, and microwave-assisted heating at 140°C for 30min. Cool to room temperature after the reaction, filter, and purify the filtrate through a neutral alumina column, elute with pure acetonitrile, and separate 4 bands, 1 band is light yellow, 2 bands are dark reddish brown, 3 bands are light yellow bands, and 4 bands are dark reddish brown . Pure acetonitrile was eluted, 1 band and 2 bands were collected, 3 bands were collected for elution with acetonitrile:methanol=50:1, which was t...

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Abstract

Theinvention provides an alkynyl containing ruthenium complex, and also relates to a synthesis method and application of the alkynyl-containing ruthenium complex. The alkynyl-containing ruthenium complex is a new type of ruthenium complex, and alkynyl is introduced into the DPPZ type ruthenium complex through Sonogashira coupling reaction, and is favorable for promoting the transmembrane absorption effect of drug molecules, improving the probability of drugs entering cells and enhancing the medical efficacy while lowering the toxic and side effects of the drugs. The alkynyl-containing ruthenium complex provided by the invention has significant anti-tumor activity, especially anti-breast cancer activity, provides a new idea for molecule design of future anti-tumor drugs, can also be used asa fluorescent probe, and thus has broad application prospects in the field of medicinal chemistry.

Description

technical field [0001] The invention relates to a ruthenium complex, in particular to an alkynyl-containing ruthenium complex, and to a synthesis method and application of the alkynyl-containing ruthenium complex. Background technique [0002] Currently, antitumor drugs used in clinical chemotherapy or adjuvant therapy have good curative effect on some tumors, and most drugs are limited to the remission of the disease. Clinical studies have shown that most anticancer drugs have poor selectivity to cells. While acting on cancer cells, normal cells and tissues are also subject to strong toxic and side effects, which affects clinical application. Therefore, new drugs are explored to improve efficacy and reduce Small side effects are the future development trend. Ruthenium (II) metal complexes have the characteristics of high efficiency, low toxicity, easy absorption, and fast excretion. They are recognized as the most potential anti-tumor drugs in research and clinical fields ...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06A61P35/00
CPCA61P35/00C09K11/06C07F15/0053C09K2211/185B01J31/2295B01J2531/824C09K2211/1074
Inventor 梅文杰汪保国
Owner GUANGDONG PHARMA UNIV
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